Stereoselective synthesis of complex polycyclic aziridines: use of the Brønsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency

Abstract

A concise synthesis of a highly functionalized intermediate lacking only C10 of the mitomycin backbone is described. The key to this development is the Brønsted acid-catalyzed aza-Darzens reaction used to forge the cis-aziridine. Additionally an oxidative ketalization fortuitously occurs during the quinone–enamine coupling step, leading to an orthogonally protected hydroquinone.